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From what I can see the WebSense filter blocks sites according to broad definitions of the content of the sites. So if a site is associated with other sites by name only then that site is also blocked.
Now image if books in the library were "filtered" in the same way. The other day a book from our library was brought to the administrations attention "My Mom's Having a Baby" innocuous
Am I proposing that kids be given open access to everything at school, no of course not. What I am saying is that web filters are a very blunt tool and do not do a very good job. They give the illusion of safety with out teaching kids how to be safe on the web.
If you teach swimming, kids have to jump into the pool.